Not Such An Outcast
by Girlonfirre
Summary: It is now their senior year of high school, Elena is so excited to get out of mystic falls and get away from the grief that surrounds her life. While Damon Salvatore is living his life to the fullest with booze, girls, and a lot of money. Damon's friend's sees them interact and decided to place a bet on whether Damon can get Elena to sleep with him...
1. Chapter 1

**Not Such An Outcast**

 **Chapter 1**

As the morning sun streamed through the airy curtains, Elena Gilbert rolled over to face her clock. Seeing as how she had thirty minutes to get to school, she decided it was best that she got up. So she walked into her bathroom and did all of the usual morning routine stuff that she normally did and then threw on a random outfit and went downstairs.

Scanning the house, she came to the conclusion that she was alone and that her Aunt must not have come home last night. Sighing, she grabbed a banana and a granola bar and walked out of the front door. Elena stared blankly at the black suburban in her driveway for a good two minutes and then decided that she would walk to school. Again.

 _Yeah maybe next time I'll even be able to-_

 _Never mind._

* * *

First period began like it had for the last three years; the teacher drags on for the entire class on what they hope to achieve during the year and people get all excited over being in the same class as their friends. Elena, however, was sitting in the back corner with her head facing towards her tattered copy of _The Great Gatsby_.

"Uh Elena Gilbert?" She looked up towards Mr. Clarke, her English teacher for the year, "You'll be over there next to Mr. Salvatore, okay?"

Elena felt a lump of nervousness gather in her throat as she attempted to gulp it down. Slowly, she brought her belongings to the seat in the front of the class. A couple of kids in the back, along with Damon Salvatore, started to chuckle as she sat down and pushed her glasses up her nose. Damon hopped into his seat like he was excited to sit next to her, which he was. But, there is a problem. One minor problem. Damon Salvatore was the most popular guy in school, the ladies' man, the school's number one asshole.

Damon flashed his white smile and winked at Elena, who was mentally freaking out. Elena hated this guy, this obnoxious, selfish, rich, annoying-

She could negatively describe Damon all day. Instead, she decided to turn around and forget about the world around her and transfixed herself on her book.

* * *

 _Almost done with the day_ , Elena thought. She sighed and ate her crappy school lunch just when something happened that she never thought would EVER happen. All of a sudden, Damon situates himself next to Elena and grins at her before taking a bite of sandwich.

"How's your day going, Gilbert? Missed you this summer," Damon said as he watched Elena struggle to comprehend him talking to her.

"Uh. Uh." Elena mumbled, "Fine, and okay."

Damon snickered and glanced at his buddies across the lunchroom. All of them, including Elena's former best friends, Caroline and Bonnie, gave him a thumbs up and laughed uncontrollably.

"You're cute. Did you know that?" Damon smirked. Ah, that famous Salvatore smirk. Both Damon and his brother, Stefan did that same mesmerizing, incredible smirk. "I bet you did know that. You just don't want to admit it."

Elena's eyes widened and she continued to eat her salad. Damon then removed her glasses from her face and pushed her hair out of her face.

"What are you doing? Why are you touching me?" Elena brushed Damon off of her and inched over to the other side of the lunch table. Of course, Damon followed her. It wasn't like Elena had friends sitting at the table with her, she didn't have friends.

"Woah, woah. Chill Gilbert," Damon surrendered himself and giggled. "I was just thinking, maybe since we are seat buddies now… We could get to know each other a little better." He winked at Elena and immediately saw her face change from annoyed to confused to angry.

"Please. Get away from me now," Elena munched on the lettuce and Damon just wouldn't give up.

"I'm not leaving until you at least agree to get a coffee with me after school?" Damon questioned while putting his arm around Elena. He obviously must be joking. He wouldn't try and get with a girl like Elena. Little innocent Elena, who was good in school, followed all of the rules, and didn't have any friends. Damon would NOT go for a girl like her…

"If it'll get you to leave me alone, then fine. Now. Go away," Elena, irritated, moved to the other side of the rectangular table as Damon walked away giving his table a thumbs up and sat down at his table.

* * *

"I don't think your gonna win," Mason laughed as he pat Damon's back and took a bite of his sandwich.

"I got her eating out of the palm of my hand," Damon smirked and continued to laugh with his buddies.

* * *

It was the last period of the day and Elena was already tired of school. She hated the fact that she had to pretend that everything was alright, when it wasn't. She missed her family, the way it used to be. The way her mother used to get up every morning to make her breakfast and lunch, and the way her dad used to force her to watch football with him every super bowl. She also missed the way her and her brother used to play board games at the family's lake house until they couldn't keep their eyes open they were so tired.

And, to top of this horrible day, she had a date. A DATE! A date with freakin' Damon Salvatore. The school's rich bitch who always got what he wanted because he was the perfect child. He was not! If only she could get out of this stupid mess before she looks even more foolish then she already does on a normal day. Turns out, Damon was in all of her classes and, even better, her locker was right next to his!

Elena had a plan. She was going to use the bathroom right before class ended, then she would skip the ending of last period, go to her locker, and get a head start walking home. It was about five minutes before the end of the period and she raised her hand.

"Can I go to the bathroom?"

"Sure," Mrs. Hollander went back to drawing on the chalkboard.

Elena grabbed her bag and snuck out, heading to her locker. She dropped her new, crappy books into her skinny compartment that the principal thought was enough space. Elena then hurried out of the door and started walking.

 _Yes,_ she thought, _I made it out._

* * *

She was about two minutes in when the bell sounded throughout the school and students shuffled out of the building and into their cars or buses.

"I can't find her," Damon whispered into his phone to his friend Mason.

"Maybe she went home early," Mason suggested.

"Wait, she did leave class to go to the bathroom. Maybe, she left and went home to make sure I didn't know where she was," Damon thought while slamming his black Cadillac's door.

"Woww, go get 'em tiger. You'll find her," Mason smiled through the phone.

"Dude, do you think she will actually do it? I mean, she's a dork. She doesn't seem like the type that would have sex 'till marriage," Damon laughed and started up the car.

"She is a dork, and she probably just wants attention. Just… follow through with the bet, alright? Do anything to make it happen, make her fall in love with you if you have too," Mason said.

"Okay, okay. I'm on my way to her house," Damon stated and hung up.

* * *

Elena was strolling down the sidewalk when a black Cadillac stopped right next to her.

 _Oh shit…_

 _That's Damon's car._

 _Does he know I skipped the last part of last period to not see him?_

"Hey Gilbert? Where's your car?" Damon exclaimed.

"Don't have one, not all of us have a rich daddy who gets us whatever we want," Elena snapped.

"Whoa…" Damon acted surprised and extended his arm to open the passenger door. "Get in, I got you."

"No. I don't like being in the car," Elena rambled on and kept walking with Damon following her.

"What about coffee? Don't you wanna get some? I'll pay," Damon made his famous smirk and left the door open.

"I'm not getting in the car," Elena said and crossed her arms.

"Why not? Do you have a fear of cars or something?" Damon asked.

"No, it's just… You wouldn't understand," Elena mumbled.

"Fine, where is your house? I'll drive to it, with you walking, and then we will WALK to Rook, okay?" Damon spoke softly.

"Okay, I guess. My house is a few houses up," Elena said and continued walking.

* * *

"Are you gonna tell me why you wouldn't get in the car, Elena?" Damon asked while stuffing his hands in his black jeans.

Elena was surprised he called her by her first name, "You wouldn't understa-"

"How are you so sure I wouldn't understand?"

"Because, you are too perfect. And you have the perfect life with absolutely no problems in it," Elena pushed up her glasses.

"What makes you so sure that I have no problems in my life?"

"I don't know, you act like you don't. What kind of problems do you have?" Elena was actually curious to know if the pretty boy had problems in his perfect life.

"I'm just a good actor I guess. If you share yours, I guess I'll share mine," Damon was being an actual person and it was surprising Elena. He had never acted like a genuine human being but now, he was different. He was _real_.

"I've never really told this before though…" Elena murmured.

"Elena, you could trust me," Damon smiled and she saw his beautiful white teeth.

"How do I know if I can?" Elena started, "You are the most popular kid in our school, you and your brother. You may tell everyone…"

"I'm not who you think I am, Elena," Damon said.

"Okay then… I miss my family," Elena began.

"What do you mean? Don't you live with them?" Damon questioned.

"No. It all started in sophomore year. We were going to our family's lakehouse and it was raining really hard." Elena started to feel a blob of saltwater in her eyes. "Well, our car totally hydroplaned off of Wickery Bridge and the car started to drown." A lump the size of a meatball gathered in Elena's throat. "Some Sumerians saved me and my brother, but my mom and dad…" Elena started to sob deeply. "They drowned and…"

"Oh my god. I'm so sorry, Elena," Damon almost started to cry at this. He had no idea what it was about her that made her different but he just realized now, _she had no family._ "Don't you have your brother though?"

"Well, yes," Elena sniffled. "But, he was s-so overwhelmed with grief that he turned to drugs. A-and he had to go to rehab."

Damon was shocked and speechless. This girl, this poor girl, lost her entire family. He didn't know what to do so he put his protective arm over her weak shoulder. She took off her glasses to wipe her face.

Elena looked up at him and he was staring at her.

 _Wow, she is gorgeous. How did I not notice her beautiful brown eyes before? She's beautiful on the inside and the outside._

 _What is going on? Why is he being so supportive? He's not supposed to have a kind heart, he's supposed to be the school's jerk. And WHY is he looking at me like that? Did I have something on my face? Oh god._ Elena looked away and wiped her face again with her sweater to see nothing on it.

"I'm so sorry, Elena. Do you live alone?" Damon asked and opened the door to Rook, the coffee shop.

"No, I live with my Aunt Jenna…" Elena said and walked to the counter with Damon's arm still around her.

"Oh, well that's good. I mean- nevermind." Damon mumbled and put both of his hands in his pockets. "What do you want?"

"I guess I'll have a regular coffee with no sugar and cream," Elena said and put her glasses back on, sort of missing his arm around her shoulder.

"Really? You don't strike me as the type of girl that would have straight coffee. You're like me," Damon smiled and ordered two black coffees.

"I don't really seem like what everyone expects me to be," Elena said and grabbed the coffee cup and started towards a small lounging area.

"True. So…" Damon said.

"Tell me about your _problems._ " Elena sipped her warm coffee and settled on a comfy brown couch with Damon.

"Well, to start off, I don't have the perfect life," Elena huffed and chuckled a bit.

 _There it was. That smile. He's never seen her smile before. Her pearly white, straight teeth were shining and he almost choked on his sip off coffee. He was one of the most beautiful girls he has ever seen…_

"You have a beautiful smile, Elena," Damon complimented her.

Elena glanced at him to see him staring at her. She put down her coffee and replied, "Thank you."

"Your welcome," Damon grinned at her.

"Okay, now tell me why you have such an 'oh so awful' life." Elena rested her head on her elbow.

"My dad is an asshole. He takes care of us with money and stuff, but he is such an asshole to my family. My mom if a great mom and I don't know how she is handling this but I know me and my brother are sick of it, and, never mind," Damon explained.

"Oh. Well maybe you should tell him how you feel. Sort of like an intervention," Elena supposed.

"I don't know… My brother and I don't really talk to him that much. He used to abuse us when we talked to him too much when we were younger…" Damon exclaimed

 _WHAT DID I JUST DO? I JUST TOLD THIS GIRL I BARELY EVEN KNOW THAT MY DAD USED TO ABUSE ME! WHAT IF SHE TELLS SOMEONE, MY DAD WOULD KILL ME!_

"Oh my god. I'm so sorry about that. Did you do anything that would make him do that to you?" Elena questioned, her eyes as open widened.

"No. He drinks heavily and didn't really know what he was doing, I think." Damon said and took a gulp of his warm, comforting drink.

"He had no excuse for doing that, you know that, right?" Elena gazed at him concerned.

"Yeah, I guess. Anyways, can we get off of this topic? It's sort of depressing," Damon asked and giggled a bit.

"Sure, umm. What do you wanna talk about? You're the one who wanted to go on a date with me, seat buddy," Elena smirked and looked around the room to see a handful of other couples together, talking, studying, eating, and drinking.

"How about… What's your favorite color?" Damon laughed because he had NO IDEA what to say to this amazing girl. This was so strange for Damon. He never _did not_ know what to say to a girl before. He usually talks about things that he can't remember because his mind is blank, his head if filled with smoke because apparently Elena was talking to him.

"Well, you really don't know what to say, do you?" Elena was laughing, "If you really _do_ want to know, it's red."

"That's my favorite color too, I also like black. That sounds kind of goth, but whatever." Damon and Elena were both laughing.

Just then, there was a moment of pure silence. Damon and Elena were both staring at each other and smiling. It was almost magical, someone would say.

All of a sudden, Damon's phone was ringing. The obnoxious tune was coming from his pocket.

* * *

"Sorry, I'll be right back," Damon said apologetically and walked away.

"What's up? I'm on the date," Damon asked, almost annoyed that he had to leave that gorgeous, innocent girl on the couch by herself, like she's been for a couple years now.

"Did you guys have sex yet? It normally doesn't take that long for you," Mason said.

"No, I think I'm gonna wait a few more dates…" Damon was saying and trailing off in his own mind with pictures of Elena in his head.

"Aw, you better follow through, Damon. We can't lose this bet, the girls would win and we don't want that do we?" Mason sounded almost angry.

"Okay, okay. I mean, there's things about her I would never even thought of. She isn't that bad, Mason," Damon said.

"Are you starting to like this dork, Damon?" Mason asked, laughing a little.

"No! I mean, I don't know… No, I'm not!" Damon mumbled and held his head that now started to ache.

"You _better_ not, it'll ruin our rep…" Mason emphasized himself to make himself clear.

"Alright…" Damon hung up, rolled his eyes, and started back towards Elena.

* * *

 **Hope you guys liked Chapter 1. If you like it or if you want to give me some suggestions or corrections, leave a review or PM me**

 **-girlonfirre**


	2. Chapter 2

**Not Such An Outcast**

 **Chapter 2**

 _Wet._

 _No air._

 _Suffocating._

 _Nothing filling her lungs other than water._

 _Elena choked, repeatedly._

 _Her lungs were going to give out._

 _The last thing she saw was her brother. He was banging on the window. But, then his arm froze._

 _Elena blacks out._

Elena gasped for air once she heard the nagging alarm clock that signaled her to get up for her second day of school.

She floated to the bathroom in her pajamas, half asleep, and showered. After Elena looked decent, she went to get breakfast. Walking downstairs, Elena discovered her hung over Aunt on the stool with her head over the counter.

Elena picked up her usual banana and granola and headed towards the door, kissing her Aunt's head, and leaving. On her way out, Aunt Jenna moans and falls off the stool.

"Aunt Jenna!" Elena rushed over towards her drunken Aunt, "Are you okay?"

Aunt Jenna moans, "I just want to sleep. Let me sleep! Let me sleep!"

"Okay, okay," Elena drops her Aunt back on the tiled floor and takes off out the door.

When Elena got to school, she filed into the building and went to her locker. _Was it weird she was looking forward to seeing Damon Salvatore?_

Of course, he was sitting there, pretending to arrange things in his locker just so he could see her. Damon pretended he did not see her and continued to mingle with his friend, Mason Lockwood. Mason nudged his shoulder and turned around to flirt with a random girl.

Damon shut his locker and gazed at the tan beauty walking towards him. "Hey Gilbert," Damon winked at Elena and leaned against his locker with his black shoes crisscrossing.

"Hey," Elena said, spinning her dial and picking up her textbooks and binders. She checked the mirror that was in her locker, trying to fix herself without Damon seeing her. _Was she attempting to look good for Damon Salvatore?_

"How's it going?" Damon asked while Mason kicked his calf. "Ahem…" Damon cleared his throat.

"It's going good, my Aunt fell this morning. She was hung over and didn't want to get up, so I left her there," Elena's eyes widened and let out a small laugh.

"Oh, wow," Damon chuckled with Elena.

"So… You just gonna stare at me? Not make some bitchy comment like you used too?" Elena was running out of things to say and didn't know what to do.

Elena and Damon started towards homeroom.

"Well, I guess I'm sorry for when I did that. I just… I didn't know you like I do now, and, you're not that bad," Damon smirked and accidentally brushed his hand against hers.

There was a moment of awkwardness and Elena immediately moved her hand, tasting the awkwardness. "Thanks, if that's a compliment," Elena and Damon laughed.

Damon held the door open for the brunette beauty and escorted her to her seat and sat at his own. Elena set her books down and looked over at the pair of enchanting green eyes that were attacking her with just a simple stare.

"What are you doing Friday? You wanna come to this party Mason's having?" Damon asked, sounding more hopeful than he should of if this whole thing was just a bet.

"I'm not really a party person," Elena tied her hair up in a loose bun.

Damon watched her like a hawk. "A little party ain't kill nobody," Damon smirked at Elena.

"I know… But I don't really fit in with your crew. Their different, and I'm nothing like them…" Elena mumbled. She did _not_ want to go to this popular party with booze and sweaty dancing couples.

"No one ever _doesn't_ fit in. It's just you have your ways of doing things and they have theirs," Damon all of a sudden got a text.

 **U better get with that girl then. It's ruining ur reputation just sitting next 2 her.**

 **-Mason**

Damon then turned around to see Mason glaring at him and he shared the glare because he was slightly angry that he didn't call her by her first name. Elena. She wasn't just some random _girl,_ she was Elena Gilbert. An innocent, depressed, lonely girl who lost her parents.

 **Idk if she will, we will have to see.**

 **-Damon**

 **Dude, don't play with me, we can't lose this god damn bet…**

 **-Mason**

 **Okay jeeze**

 **-Damon**

Damon turned his attention to Elena again.

"So, what do you say?" Damon winked and fixed himself in his chair.

"Fine… But this isn't like hardcore partying with alcohol right?" Elena asked. "By the way, where is it? I'm walking."

"Elena, honey, every party in senior year has alcohol. It's really far away… It's all the way across town, you can't walk that far, I can drive you, its fine," Damon stated with a concerned expression on his face.

"I'm walking. You could walk with me if you want," Elena exclaimed, twisting a rope of loose chocolate colored hair.

"Uh…" Damon glanced at Mason for a moment to see him all over a pair of blondes, "Sure, I guess were walking…" Damon attempted to stage a smile.

 _I guess more time to learn about Elena Gilbert._

"Aunt Jenna?! Are you home!?" Elena, very unsure of what to wear, was hollering from her bedroom for her Aunt's grown-up assistance.

She heard a moan from downstairs and followed the strange noise that was coming from her Aunt. Elena walked down the stairs to find her Aunt lying on the TV room's couch with a glass of wine in her hand.

 _Ugh, not again._

"Aunt Jenna? Can you help with something?" Elena asked softly, biting her bottom lip.

"Y-y-y-yeah honey. What do you need help w-w-w-with?" Aunt Jenna gave a drunken grin and showed her rotting teeth.

"Well, I am going to a party, and I don't know what to wear," Elena said, sitting on the end of the couch.

Aunt Jenna took a large gulp of red wine, "A party! Little Elena is growing up soo f-f-fast! Of c-c-course I'll help youu!"

Aunt Jenna stood up wearing a fluffy, lavender robe and dropped her glass of wine on the hardwood floor, "To your bedroom!"

"Alright, so what should I wear? Nothing too dressy, right? Maybe this?" Elena pulled out a chunky oatmeal sweater and a maroon scarf.

 _Whoa, I haven't worn something like this since…_

Aunt Jenna sat on the bed and gazed around the room, "Maybe a different colored room would be good. Oh, and yes! T-that's very cute!"

Elena slid on the sweater and scarf then picked out a pair of black leggings and some black boots. She then went to the bathroom to check out her hair. It was a frizzy mess.

Elena opened her cabinet that was under her sink, looking for her old curling iron.

After finishing the last curl, Elena went under her sink again to find her makeup back. She did a little eye makeup and put some gloss on her lips.

"Finished. Aunt Jenna, how do I look? Is this too much?" Elena walked out of the bathroom looking like a model. It has definitely been a while since she has gotten dressed up for an event.

"Oh my goodness, Elena… You look exactly like your mother," Aunt Jenna started to tear up, she was also a little sober, Elena thought…

"Aw, it's okay," Elena put her arm around her Aunt Jenna's shoulder and sat with her for a few minutes before she stopped sobbing.

"Oh, I forgot to give you something. I got you these, they match your prescription," Aunt Jenna dug in her robe's pocket for a container that said "Acuve."

"Oh my god! Did you get me contacts?" Elena screamed at the top of her lungs. She hasn't been that happy since before her parents died. "Thanks so much, Aunt Jenna! I love you."

"Your w-welcome, now, go to the bathroom and try 'em out. After that, go downstairs. In the cabinet with the alcohol, there is some tequila. In the glasses cabinet there is a shot glass, take a shot before you go to this party, just so you're prepared, it'll also loosen you up," Aunt Jenna smiled and lay her head on Elena's pillow.

Elena laughed and did as she was told. She went to the bathroom and took off her glasses. Everything was blurry, but then she placed the contacts in her eyes along with the liquid to stop it from hurting and was extremely overjoyed. She always hated her glasses even though they were adorable Vera Wang turtle shell patterned. Elena loved her new look without her glasses.

All of a sudden, Elena heard the doorbell ring _. It must be Damon._

Elena rushed down the stairs and opened the door to find a smirking Damon with his leather jacket hanging off his shoulder.

"You look… Amazing, Elena. Where's your glasses?" Damon asked, walking in the house.

"Aunt Jenna got me contacts," Elena said surprised, "One more thing." Elena walked into the kitchen and was almost shocked at what she was about to do. She opened the cabinet and took out the Patron and two shot glasses.

"Whoa, Gilbert is a little risky tonight isn't she?" Damon smiled and waited eagerly for his shot.

"Just need to 'loosen up,'" Elena quoted her Aunt and filled up the two shot glasses.

Elena handed one to Damon, Elena clacked hers against his and said, "Cheers to… Loosening up."

They both took the shots. Elena's faced scrunched up, similar as to what it would be if she tasted a lemon, and she coughed.

"Was that your first time drinking alcohol?" Damon acted perfectly fine and giggled at Elena's reaction.

"No, I had a few tastes of my parents' when I was younger but that was about it," Elena confessed and laughed at herself for being so _lame_.

"Aw, little Gilbert is finally coming out of her shell," Damon winked and grinned at Elena and she felt a burning in her chest. She didn't know if it was from the alcohol or if it was from the fact that she was going to a party with Damon Salvatore.

"Oh shut up," Elena was laughing when she came out of her zone and lightly punched Damon on the shoulder.

"C'mon, since were walking were gonna be late if we don't go now," Damon smirked and reached out for Elena's hand.

The one shot made Elena a little buzzed because turns out, she's actually a total light-weight.

They were walking down the sidewalk with their hands in each other's talking about how the school has the worst teachers.

"I mean, the only good one is that new one, Mr. Saltzman," Elena laughed and stared ahead at the big Oak tree.

Damon nodded his head, "I agree with you there, but he wants us to call him by his first name, Alaric."

"What kind of a name is that anyway?" Elena burst into giggles, keeping her hand in his.

"Who even knows?" Damon smiled and glimpsed at Elena.

 _It's like she is a whole new person. What happened? She looks so beautiful it's driving me insane. I don't know if I want to follow through with this bet on their terms, but maybe mine._

By the time Elena and Damon got to the house the party was at, it was almost pitch black. They could hear the loud music down the street. There was lights flashing and people out on the front lawn chasing each other, obviously drunk.

When they walked into the house, it was as if the whole entire party was put on pause. They all stared at Elena in confusion until some girl, her name was Chelsea Winters, Elena thought, walked up to her.

"Who the hell are you? Do you even go to Mystic Falls High?" Chelsea snottily asked.

Her tight crop top and shorts made it look like she was from a Playboy magazine.

"I'm Elena Gilbert, and _yes_ I do go to Mystic Falls High School," Elena answered back just as rudely.

"Oh wow. You went from weird ass dork to some hot bitch. I like you. Come have a drink with me," Chelsea sneered and grabbed Elena from Damon.

On the way to the kitchen, twenty guys must have squeezed her ass. _Horny little jerks_ , Elena thought.

 **So I didn't leave off with a cliff hanger this time. But, upcoming chapter is definitely going to have some REAL Delena action going on. Do you guys Damon is gonna follow through with the bet on the girl's terms, or his? Should I add Katherine to this story? Tell me what you think!**

 **By the way, if you have ever read "This Is The Start Of Something Beautiful" by glitterintheairr? Well, if you haven't, you should totally read it! My sister actually wrote it, and left off with such a cliff hanger. She stopped updating because she thought no one liked it :( I loved it and she said I can continue it! Anyways, go look at it because I'm gonna write the rest of the story!**

 **-girlonfirre**


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